Benzyl Bromide → HCID 59553892, compound

HRID 1170924Notes

Reaction equation

HRID 1170924 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])=[N:7][C:6]=2[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CC(C)=O>[CH2:34]([O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:8]1[N:9]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](=[O:12])[C:11]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]=2[N:7]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135966007HCID 135966007, compound

Product 1

HCID 59553892HCID 59553892, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Chloro-2-(2-methoxy-phenyl)-3-phenethyl-3H-pyrido[4,3-d]pyrimidin-4-one was subjected to the same deprotection conditions found in the final step of Example 1 to provide the desired 5-chloro-2-(2-hydroxy-phenyl)-3-phenethyl-3H-pyrido[4,3-d]pyrimidin-4-one. A mixture of 5-chloro-2-(2-hydroxy-phenyl)-3-phenethyl-3H-pyrido[4,3-d]pyrimidin-4-one (88 mg, 0.233 mmol), potassium carbonate (64 mg, 0.466 mmol, 2 equiv.) and benzyl bromide (0.029 mL, 0.245 mmol, 1.05 equiv.) in 2 mL of acetone was heated to reflux overnight. The reaction mixture was cooled to RT, filtered through celite, concentrated and the residue purified on preparative TLC plate using 1:1 ethyl acetate:heptane to give 95 mg (87%) of the desired product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationfiltered through celite,
  4. concentrationconcentrated
  5. customthe residue purified on preparative TLC plate

Sources & evidence

ORD record
ord-fc4dc36ad2e2428eb97b36aeb7db020c
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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